Port Royal was a city situated on the end of an 18-mile long sand spit known as the Palisadoes, at the mouth of the Kingston Harbour, in south-eastern Jamaica. Founded in 1518, it rapidly grew to become the most important trading post in the Caribbean Sea due to its strategic position on the trading routes between the New World and Spain. When England officially appointed privateers to raid enemy ships in the Caribbean, as a part of its defence strategy, pirates from around the world congregated at Port Royal to legitimize their trade. Soon Port Royal became a notorious hub for pirate activity, gambling, prostitutes, and booze leading it to be branded as "the wickedest city on earth".

Port Royal’s glory days didn’t last long. At the height of its glittering wealth on June 7, 1692, a massive earthquake shook Jamaica. The sea swallowed the town killing 2,000 people and wounding 3,000 others. The local clergy ascribed the destruction of Port Royal as God's punishment on the people for their sinful ways. Today, the area is a shadow of its former self with a population of less than 2,000 and little to no commercial or political importance.

The first Europeans to land on Jamaica were the Spaniards under the leadership of Christopher Columbus in 1494. Spain maintained control over the island for 146 years, until the English invasion of 1655. As a solution to their defence concerns, the then Governor of England invited pirates to Port Royal giving them official “letters of marque” to go after Spanish ships and settlements. The strategy proved to be so successful that Spain was forced to continually defend their property. With ships frequently looted, it struggled to provide its colonies with manufactured goods on a regular basis.

Port Royal meanwhile flourished. Between 1655 and 1692, it grew faster than any town founded by the English in the New World. At its height in 1692, the town had a population of 6,500 and 2,000 buildings densely packed into 51 acres. Its free-spending inhabitants threw away their money in gambling, whoring and drinking, and the town developed a reputation as a den of wickedness and godlessness.

When Charles Leslie wrote of Port Royal in the 1660s, he included the description: “Wine and women drained their wealth to such a degree that... some of them became reduced to beggary. They have been known to spend 2 or 3,000 pieces of eight in one night; and one gave a strumpet 500 to see her naked. They used to buy a pipe of wine, place it in the street, and oblige everyone that passed to drink.”